ATE479768T1 - METHOD FOR THE REGIOSELECTIVE N(5)-FORMYLATION OF (6S)-5,6,7,8-TETRAHYDROPTEROIC ACID AND DERIVATIVES THEREOF - Google Patents

METHOD FOR THE REGIOSELECTIVE N(5)-FORMYLATION OF (6S)-5,6,7,8-TETRAHYDROPTEROIC ACID AND DERIVATIVES THEREOF

Info

Publication number
ATE479768T1
ATE479768T1 AT07700120T AT07700120T ATE479768T1 AT E479768 T1 ATE479768 T1 AT E479768T1 AT 07700120 T AT07700120 T AT 07700120T AT 07700120 T AT07700120 T AT 07700120T AT E479768 T1 ATE479768 T1 AT E479768T1
Authority
AT
Austria
Prior art keywords
formula
formyl
compound
added
regioselective
Prior art date
Application number
AT07700120T
Other languages
German (de)
Inventor
Achille Arini
Raffaela Coppolecchia
Antonio Tognini
Raffaela Manzotti
Fabrizio Marazza
Original Assignee
Cerbios Pharma Sa
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cerbios Pharma Sa filed Critical Cerbios Pharma Sa
Application granted granted Critical
Publication of ATE479768T1 publication Critical patent/ATE479768T1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
    • C12P17/182—Heterocyclic compounds containing nitrogen atoms as the only ring heteroatoms in the condensed system
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/10—Transferases (2.)
    • C12N9/1003—Transferases (2.) transferring one-carbon groups (2.1)
    • C12N9/1014—Hydroxymethyl-, formyl-transferases (2.1.2)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y201/00—Transferases transferring one-carbon groups (2.1)
    • C12Y201/02—Hydroxymethyl-, formyl- and related transferases (2.1.2)
    • C12Y201/02005—Glutamate formimidoyltransferase (2.1.2.5)

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Genetics & Genomics (AREA)
  • General Health & Medical Sciences (AREA)
  • General Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Microbiology (AREA)
  • Biotechnology (AREA)
  • Biomedical Technology (AREA)
  • Molecular Biology (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Steroid Compounds (AREA)

Abstract

The process according to the invention for regioselective N(5)-formylation of (6S)-5,6,7,8-tetrahydropteroic acid and derivatives thereof which are defined in formula (I) is characterized in that an aqueous buffer solution having a pH of from 6.5 to 7.5 is added to a mixture of a compound of the formula (I), an antioxidant and a formyl donor in a reaction vessel; an inert gas is blown through the resulting suspension; then an aqueous solution of a base is added dropwise or in portions with constant stirring until a clear solution which has a pH between 6.5 and 8.3 is formed; then a recombinant monofunctional glutamate formyl transferase, abbreviated to rGFT, i.e. the enzyme, is added in an aqueous buffer solution defined above; then the temperature is increased to a range of 30°C to 45°C and the reaction mixture is allowed to react until at least 95% of the formyl has been transferred from the formyl donor to the compound of the formula (I), - then the resulting reaction mixture is cooled to a temperature of from 0°C to 5°C; then an aqueous solution of a mineral acid is added dropwise until a pH of from 2.7 to 3.1 has been attained, which precipitates out the crude compound of the formula (II); the stirring is continued over at least 1 hour in order to complete the abovementioned precipitation, and the crude compound of the formula (II) is obtained.
AT07700120T 2006-01-19 2007-01-18 METHOD FOR THE REGIOSELECTIVE N(5)-FORMYLATION OF (6S)-5,6,7,8-TETRAHYDROPTEROIC ACID AND DERIVATIVES THEREOF ATE479768T1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH00083/06A CH696699A5 (en) 2006-01-19 2006-01-19 Process for regioselective N (5) -Formylierung of (6S) -5, 6, 7, 8-Tetrahydropteroinsäure and derivatives thereof.
PCT/CH2007/000022 WO2007082402A2 (en) 2006-01-19 2007-01-18 Process for regioselective n(5)-formylation of (6s)-5,6,7,8-tetrahydropteroic acid and derivatives thereof

Publications (1)

Publication Number Publication Date
ATE479768T1 true ATE479768T1 (en) 2010-09-15

Family

ID=38287969

Family Applications (1)

Application Number Title Priority Date Filing Date
AT07700120T ATE479768T1 (en) 2006-01-19 2007-01-18 METHOD FOR THE REGIOSELECTIVE N(5)-FORMYLATION OF (6S)-5,6,7,8-TETRAHYDROPTEROIC ACID AND DERIVATIVES THEREOF

Country Status (6)

Country Link
EP (1) EP1974047B1 (en)
JP (1) JP2009523740A (en)
AT (1) ATE479768T1 (en)
CH (1) CH696699A5 (en)
DE (1) DE502007004915D1 (en)
WO (1) WO2007082402A2 (en)

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB721742A (en) * 1950-02-17 1955-01-12 Research Corp Improvements in or relating to compounds having vitamin activity and methods of preparing them
US2824045A (en) * 1954-03-19 1958-02-18 Merck & Co Inc Microbial production of folinic acid
CH673459A5 (en) * 1987-05-15 1990-03-15 Eprova Ag
ATE139799T1 (en) * 1989-12-11 1996-07-15 American Cyanamid Co METHOD FOR PRODUCING OPTICALLY PURE DIASTEREOISOMERS OF TETRAHYDROFOLATE COMPOUNDS
US5153309A (en) * 1990-07-27 1992-10-06 The United States Of America As Represented By The Department Of Health And Human Services Process of making tetrahydropteroylpoly-l-glutamic acid derivatives
US5198547A (en) * 1992-03-16 1993-03-30 South Alabama Medical Science Foundation, Usa Process for N5-formylating tetrahydropteridines

Also Published As

Publication number Publication date
DE502007004915D1 (en) 2010-10-14
JP2009523740A (en) 2009-06-25
CH696699A5 (en) 2007-10-15
WO2007082402B1 (en) 2008-01-03
WO2007082402A3 (en) 2007-11-15
WO2007082402A2 (en) 2007-07-26
EP1974047A2 (en) 2008-10-01
EP1974047B1 (en) 2010-09-01

Similar Documents

Publication Publication Date Title
ES2594603T3 (en) Selective and reversible inhibitors of ubiquitin-specific protease 7
US9650621B2 (en) Proteolytic inactivation of select proteins in bacterial extracts for improved expression
US8586570B2 (en) Sox-based kinase sensor
Faggiano et al. The missing links to link ubiquitin: Methods for the enzymatic production of polyubiquitin chains
SG10201804238TA (en) Enhanced deposition of chromogens utilizing pyrimidine analogs
ATE457981T1 (en) 3-AMIDO-1,2-BENZISOXAZOLE DERIVATIVES, PRODUCTION PROCESS AND USE THEREOF
DK72587D0 (en) PROCEDURE FOR ENZYMATIC DIPEPTID PREPARATION
ES8306182A1 (en) A process for enzymatic replacement of the B-30 amino acid in insulins.
CN105503879B (en) A kind of method of immobilization albumen
BR0213779A (en) Isolated nucleic acid molecule, vector, host cell, and, method for the preparation of a chemically fine compound
DE502007004915D1 (en) PROCESS FOR REGIOSELECTIVE N (5) FORMATION OF (6S) -5,6,7,8-TETRAHYDROPTEROIC ACID AND DERIVATIVES THEREOF
SG158739A1 (en) Aggrecanase molecules
US11708375B2 (en) Reagents for reversibly protecting biological molecules
US20180258077A1 (en) 5-sulfanylhistidines and their disulfides and method of preparation thereof
DK149824C (en) PROCEDURE FOR ENZYMATIC REPLACEMENT OF B-30 AMINO ACIDS IN INSULINES
Hennessy et al. Creation of an engineered amide synthetase biocatalyst by the rational separation of a two‐step nitrile synthetase
CN103154019A (en) Method for producing surfactin and salt thereof
EP2151499A3 (en) Processes for the preparation of phosphatides
MX2023014874A (en) Uses and processes for enzymatic nucleic acid synthesis.
US20200017479A1 (en) Novel 5-acylsulfanyl-histidine compounds as precursors of the corresponding 5-sulfanylhistidines and their disulfides
JP5704481B2 (en) Nucleic acid detection kit
DK0567323T3 (en) Improved method of preparing cephalosporins
US11643673B2 (en) Functionalised cyclic dithiocarbamate synthesis method
ATE473990T1 (en) METHOD FOR SYNTHESIS OF IBANDRONATE SODIUM
Cereda et al. Molecular recognition between Azotobacter vinelandii rhodanese and a sulfur acceptor protein.